This happened a few months ago and I have thought about nothing else since, was an incredible experience.
I have been dressing since I was a boy, wearing my older sisters sexy underwear and clothes. I've always enjoyed having sexy satin/silky lingerie dressing in them and enjoying a masturbation to some cross dressing porn.
I suddenly started thinking about dresses and then makeup and before I knew it when my wife was away for the day or overnight to a friends I was dressing and calling myself Tracey and loved being around the house fully dressed in heels, nails, wig and sexy clothes, sometimes I wouldn't even cum , this was different from what I was doing previously and felt different.
I then took to taking photos of myself and eventually thought I would share on a website. I was overwhelmed by the amount of nice comments I got and how nice I looked dressed as a female. My confidence just grew from there and loved this male attention towards me as Tracey. All the guys obviously wanted to meet and a few other dressers gave me pointers and I knew from the internet caution was required.
I eventually got talking to a few guys regularly and separated out timewasters from those guys who really have an interest in cross dressers and a real appreciation. I agreed to meet a guy who had sent his photographs, was married and ticked all the boxes. A lot of the other dressers I spoke to suggested guys just came in and wanted either to shoot In your mouth or fuck you with very little foreplay and unfortunately for the first few meets that was the situation. The first guy I met was nice and introduced me to poppers which was amazing. He had a 7" cock, after me sucking him and him sucking me he put a condom on, put lube on his cock and put some around my hole. He then took a little bottle from his jacket pocket that was on the floor next to the bed an proceeded to hold one of my nostrils and invited me to sniff hard which I did and then did the same with the other nostril. I suddenly felt a warm feeling in my head and very relaxed. I lay there and watched as he lifted my skirt and lay on top of me motioning his cock in to my hole, before I knew it he was riding me, he handed me the bottle again and I took a few sniffs and the warm feeling returned. I couldn't believe here I was as Tracey on our bed and a guy on top of me fucking me. He kept thrusting and eventually shot his cum in to the condom. It was an amazing experience and my first introduction to poppers and anal sex.
I bought some poppers and lube, this was the routine for the next few meets either a guy fucking me or shooting in my mouth.
My story was really to tell of my last meet which was so much more. I always make a tremendous effort to be dressed sexy and to look very attractive as Tracey. I started speaking to this guy Mike and we got on really well, flirting with each other online. He came across very gentle and that was attractive. There was loads of flirting not just talk of fucking.
I always have everything prepared for a meet , condoms, lube and poppers beside the bed. I like to have a drink of bacardi or vodka before meeting just to relax me, this morning I had a little more and felt very turned on and sexy.
Mike arrived and immediately I realised his photographs he had sent didn't do him justice as he was very attractive and sexy. He seemed to like the way I was dressed in a little black sexy dress with holdups, heels, my hair was nice as I had spent ages on my long wig and I smelled nice with lovely perfume.
We started kissing in the lounge and I was very aroused although my cock was tucked in to my tight thong so not to spring out, I could feel Mike was very hard as our bodies moved together as we kissed. We moved on to the sofa and continued kissing and running our hands over each other. I suddenly felt there was more to meeting guys than just letting them in sucking them or fucking them and out again, I was loving this level of kissing with tongues and how Mike was running his hands all over my dress then slowly lifting my dress and touching my cock, Mike then motioned down lifting my dress and started to lick my cock taking it in to his mouth and sucking....it was electric!
My dress zipped down the front and Mike after kissing me again for such a long time zipped my dress down a little and caressed my breasts and started to play with my nipples, I felt I was in heaven with all this gentle loving attention. Mike then started to kiss my nipples and then we kissed again for ages. I looked at the clock and Mike had been kissing me, sucking me and playing with me for 40 mins, my 5 previous meets had all been in/out in about 10 mins.
I suggested we move to the bedroom and I led him by hand in to the bedroom and turned to Mike and started to undress him , removing every part of clothing revealing a very fit body underneath. We lay on the bed and I still had my dress on with just the front unzipped a little. We kissed again and Mike caressed me all over and once again he lifted my dress going down to suck me. He moved over and handed me the poppers encouraging me to sniff some which I did. Mike then started to slide fingers in to me as he sucked me....I though I was going to shoot my load immediately and motioned for Mike to stop as I didn't want to cum too quickly although I was so turned on but this sex was incredible. Mike moved his body up and sat over my chest thrusting his 7" cock in front of my face. I licked it building up a wetness and then took it deep in my mouth, I could feel Mike getting harder and then suddenly he pulled away and handed me the poppers again but not to sniff any just yet so I just held the bottle as Mike started to move his cock around my hole teasing it, this had never been done to me before and was quite nice feeling. Mike then motioned me to take deep sniffs which I did and then he slowly moved his cock in to position and slid deep inside me …...wow this lovely gentle guy has just ploughed his cock in to me bareback.
I was stunned however it was too good a moment to spoil and felt myself wrapping my legs aound Mike and holding him tight as he continued to thrust lovingly and I felt his speed increase and suddenly he was shooting his load in me and again I was so turned on and relaxed I couldn't stop this happening.
We lay in bed ages after and both of us couldn't believe what had just taken place, even though I hadn't cum I thoroughly enjoyed and can't wait until lockdown is over to meet Mike again. x